Tag: 100-200

Iridium-Catalyzed Highly Enantioselective Transfer Hydrogenation of Aryl N-Heteroaryl Ketones with N-Oxide as a Removable ortho-Substituent was written by Liu, Qixing;Wang, Chunqin;Zhou, Haifeng;Wang, Baigui;Lv, Jinliang;Cao, Lu;Fu, Yigang. And the article was included in Organic Letters in 2018.Recommanded Product: 4-Methylpicolinonitrile This article mentions the following:

A highly enantioselective transfer hydrogenation of non-ortho-substituted aryl N-heteroaryl ketones, using readily available chiral diamine-derived iridium complex as a catalyst and sodium formate as a hydrogen source in a mixture of H₂O/i-PrOH (volume/volume = 1:1) under ambient conditions, is described. The chiral aryl N-heteroaryl methanols were obtained with up to 98.2% ee by introducing an N-oxide as a removable ortho-substituent. In contrast, no more than 15.1% ee was observed in the absence of an N-oxide moiety. Furthermore, the practical utility of this protocol was also demonstrated by gram-scale asym. synthesis of bepotastine besilate in 51% total yield and 99.9% ee. In the experiment, the researchers used many compounds, for example, 4-Methylpicolinonitrile (cas: 1620-76-4Recommanded Product: 4-Methylpicolinonitrile).

4-Methylpicolinonitrile (cas: 1620-76-4) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Recommanded Product: 4-Methylpicolinonitrile

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

On the preparation of 1-aryl-2-heteroaryl- and 2-aryl-1-heteroarylpyrroles as useful building blocks for biologically interesting heterocycles was written by Almerico, Anna Maria;Montalbano, Alessandra;Diana, Patrizia;Barraja, Paola;Lauria, Antonino;Cirrincione, Girolamo;Dattolo, Gaetano. And the article was included in ARKIVOC (Gainesville, FL, United States) [online computer file] in 2001.Reference of 28020-37-3 This article mentions the following:

A series of 1-aryl-2-pyridinyl/pyrimidinyl-pyrroles and 2-aryl-1-pyridinyl/pyrimidinyl-pyrroles were prepared by using 4+1 ring synthesis. The yields were strongly dependant on the reactivity of the starting amines. Synthetic procedures involving a 3+2 ring formation were discussed. Few 1-heteroaryl derivatives showed weak activity when tested as COX-1 and COX-2 inhibitors. In the experiment, the researchers used many compounds, for example, 3-Amino-2,6-dimethoxypyridine (cas: 28020-37-3Reference of 28020-37-3).

3-Amino-2,6-dimethoxypyridine (cas: 28020-37-3) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Reference of 28020-37-3

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Visible-Light-Promoted Copper-Catalyzed Regioselective Benzylation of Pyridine N-Oxides versus Thermal Acylation Reaction with Toluene Derivatives was written by Kianmehr, Ebrahim;Gholamhosseyni, Maral. And the article was included in European Journal of Organic Chemistry in 2018.Safety of 3,5-Dimethylpyridine 1-oxide This article mentions the following:

Copper-catalyzed visible light mediated direct C-H bond benzylation of pyridine N-oxides with toluene derivatives was accomplished by recent developments in photochem. carbon-carbon bond formation through a photo-induced bond-dissociation strategy. This visible light driven protocol has been successfully applied to a broad scope of pyridine N-oxides and toluene derivatives Furthermore, preliminary research indicates that the acylation reaction can be carried out under thermal reaction conditions. This protocol provides easy access to 2-benzyl and 2-acyl pyridine N-oxide derivatives in the presence of a copper catalyst. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Safety of 3,5-Dimethylpyridine 1-oxide).

3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Safety of 3,5-Dimethylpyridine 1-oxide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Monodisperse CuPd alloy nanoparticles as efficient and reusable catalyst for the C (sp²)-H bond activation was written by Huang, Fei;Wang, Feifan;Hu, Qiyan;Tang, Lin;Xu, Dongping;Fang, Yang;Zhang, Wu. And the article was included in Applied Organometallic Chemistry in 2021.Application In Synthesis of 2-(m-Tolyl)pyridine This article mentions the following:

Metal-catalyzed selective activation of C-H bonds is very important for the construction of a variety of biol. active mols. Supported alloy nanoparticles are of great interest in various catalytic applications due to the synergistic effects between different metals. Here, well-dispersed CuPd alloy nanoparticles supported on reduced graphene oxide (rGO) were synthesized and found to be highly efficient and recyclable catalyst for the chelation-assisted C(sp²)-H bond activation. Aromatic ketones or esters were synthesized via the cross-dehydrogenative coupling (CDC) reaction between 2-arylpyridines and alcs. or acids [e.g., 2-phenylpyridine + benzyl alc. → I (94%)]. Moreover, the catalyst was recovered and used for five times without significantly losing activity. In the experiment, the researchers used many compounds, for example, 2-(m-Tolyl)pyridine (cas: 4373-61-9Application In Synthesis of 2-(m-Tolyl)pyridine).

2-(m-Tolyl)pyridine (cas: 4373-61-9) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Several pyridine derivatives play important roles in biological systems. While its biosynthesis is not fully understood, nicotinic acid (vitamin B3) occurs in some bacteria, fungi, and mammals.Application In Synthesis of 2-(m-Tolyl)pyridine

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Trifluoromethylation of Aryl and Heteroaryl Halides with Fluoroform-Derived CuCF₃: Scope, Limitations, and Mechanistic Features was written by Lishchynskyi, Anton;Novikov, Maxim A.;Martin, Eddy;Escudero-Adan, Eduardo C.;Novak, Petr;Grushin, Vladimir V.. And the article was included in Journal of Organic Chemistry in 2013.Related Products of 116308-35-1 This article mentions the following:

Fluoroform-derived CuCF₃ recently discovered in our group exhibits remarkably high reactivity toward aryl and heteroaryl halides, performing best in the absence of extra ligands. A broad variety of iodoarenes undergo smooth trifluoromethylation with the “ligandless” CuCF₃ at 23-50 °C to give the corresponding benzotrifluorides in nearly quant. yield. A number of much less reactive aromatic bromides also have been trifluoromethylated, including pyridine, pyrimidine, pyrazine, and thiazole derivatives as well as aryl bromides bearing electron-withdrawing groups and/or ortho substituents. Only the most electrophilic chloroarenes can be trifluoromethylated, e.g., 2-chloronicotinic acid. Exceptionally high chemoselectivity of the reactions (no side-formation of arenes, biaryls, and C₂F₅ derivatives) has allowed for the isolation of a large number of trifluoromethylated products in high yield on a gram scale (up to 20 mmol). The CuCF₃ reagent is destabilized by CuX coproduced in the reaction, the magnitude of the effect paralleling the Lewis acidity of CuX: CuCl > CuBr > CuI. While S_NAr and S_RN1 mechanisms are not operational, there is a well-pronounced ortho effect, i.e., the enhanced reactivity of ortho-substituted aryl halides 2-RC₆H₄X toward CuCF₃. Intriguingly, this ortho-effect is observed for R = NO₂, COOH, CHO, COOEt, COCH₃, OCH₃, and even CH₃, but not for R = CN. The fluoroform-derived CuCF₃ reagent and its reactions with haloarenes provide an unmatched combination of reactivity, selectivity, and low cost. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethyl)nicotinaldehyde (cas: 116308-35-1Related Products of 116308-35-1).

2-(Trifluoromethyl)nicotinaldehyde (cas: 116308-35-1) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Related Products of 116308-35-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Flow Microreactor Technology for Taming Highly Reactive Chloroiodomethyllithium Carbenoid: Direct and Chemoselective Synthesis of α-Chloroaldehydes was written by Musci, Pantaleo;Colella, Marco;Sivo, Alessandra;Romanazzi, Giuseppe;Luisi, Renzo;Degennaro, Leonardo. And the article was included in Organic Letters in 2020.Recommanded Product: Phenyl(pyridin-2-yl)methanone This article mentions the following:

A straightforward flow synthesis of α-chloro aldehydes has been developed. The strategy involves, for the first time, the thermal unstable chloroiodomethyllithium carbenoid and carbonyl compounds A batch vs. flow comparative study showcases the superb capability of flow technol. in prolonging the lifetime of the lithiated carbenoid, even at -20°C. Remarkably, the high chemoselectivity realized in flow allowed for preparing polyfunctionalized α-chloro aldehydes not easily accessible with traditional batch procedures. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Recommanded Product: Phenyl(pyridin-2-yl)methanone).

Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Recommanded Product: Phenyl(pyridin-2-yl)methanone

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

O-Substituted pyridine N-oxide derivatives. I. N-(Trimethylammoniumethoxy)pyridinium compounds, a new type of choline derivatives was written by Augustinsson, Klas Bertil;Hasselquist, Hans. And the article was included in Acta chem. Scand. in 1961.Name: 3,5-Dimethylpyridine 1-oxide This article mentions the following:

Treating the N-oxides of pyridine and the picolines without solvent at approx. 120° and N-oxides of 4-picoline and of the lutidines in acetonitrile at reflux temperature with bromocholine gave the title compounds The reaction of 2,6-lutidine N-oxide was carried out at 100° in the presence of water under pressure. The N-oxide of 2,5-lutidine, prepared by H₂O₂ in AcOH, b. 149°; picrate m. 128-9° (EtOH). The 3,5-isomer b₂₃ 166-8°, hygroscopic solid (C₆H₆). Also were prepared: 75% N-(2-trimethylammoniumethoxy)pyridinium dibromide, m. 198°; 51% N-(2-trimethylammoniumethoxy)-2-picolinium dibromide, m. 196°; 14% 3-isomer, m. 175°; 50% 4-isomer, m. 190°; 67% N-(2-trimethylammoniumethoxy)- 2,4-lutidinium dibromide, m. 195-5.5°; 49% 2,5-isomer, m. 191°; 9.5% 2,6-isomer, m. 175-5.5°; 100% 3,5-isomer, m. 196.5-7°. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Name: 3,5-Dimethylpyridine 1-oxide).

3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Name: 3,5-Dimethylpyridine 1-oxide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Magnesiation of N-Heterocycles Using i-PrMgCl · LiCl and Catalytic Diisopropylamine was written by Nxumalo, W.;Dinsmore, A.. And the article was included in Synthetic Communications in 2015.Application of 644-98-4 This article mentions the following:

The direct magnesiation of various N-heterocyclic compounds with i-PrMgCl · LiCl and catalytic diisopropylamine allows for preparation of 2-substituted pyrroles, imidazole, indoles, and benzimidazoles, in moderate to good yields. The magnesiated substrates can readily undergo a Kumada-type coupling with iodo-aryls in the presence of catalytic Pd(PPh₃)₄. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Application of 644-98-4).

2-Isopropylpyridine (cas: 644-98-4) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Application of 644-98-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Discovery of 2-(2-Oxo-1-phenyl-5-pyridin-2-yl-1,2-dihydropyridin-3-yl)benzonitrile (Perampanel): A Novel, Noncompetitive α-Amino-3-hydroxy-5-methyl-4-isoxazolepropanoic Acid (AMPA) Receptor Antagonist was written by Hibi, Shigeki;Ueno, Koshi;Nagato, Satoshi;Kawano, Koki;Ito, Koichi;Norimine, Yoshihiko;Takenaka, Osamu;Hanada, Takahisa;Yonaga, Masahiro. And the article was included in Journal of Medicinal Chemistry in 2012.Formula: C11H9NO This article mentions the following:

Dysfunction of glutamatergic neurotransmission has been implicated in the pathogenesis of epilepsy and numerous other neurol. diseases. Here the authors describe the discovery of a series of 1,3,5-triaryl-1H-pyridin-2-one derivatives as noncompetitive antagonists of AMPA-type ionotropic glutamate receptors. The structure-activity relationships for this series of compounds were investigated by manipulating individual aromatic rings located at positions 1, 3, and 5 of the pyridone ring. This culminated in the discovery of 2-(2-oxo-1-phenyl-5-pyridin-2-yl-1,2-dihydropyridin-3-yl)benzonitrile (perampanel), a novel, noncompetitive AMPA receptor antagonist that showed potent activity in an in vitro AMPA-induced Ca²⁺ influx assay (IC₅₀ = 60 nM) and in an in vivo AMPA-induced seizure model (min. ED of 2 mg/kg po). Perampanel is currently in regulatory submission for partial-onset seizures associated with epilepsy. In the experiment, the researchers used many compounds, for example, 5-Phenylpyridin-2-ol (cas: 76053-45-7Formula: C11H9NO).

5-Phenylpyridin-2-ol (cas: 76053-45-7) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Pyridine derivatives are also useful as small-molecule α-helix mimetics that inhibit protein-protein interactions, as well as functionally selective GABA ligands.Formula: C11H9NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Direct Exploitation of the Ethynyl Moiety in Calcium Carbide Through Sealed Ball Milling was written by Hosseini, Abolfazl;Schreiner, Peter R.. And the article was included in European Journal of Organic Chemistry in 2020.Name: Phenyl(pyridin-2-yl)methanone This article mentions the following:

Ball milling of calcium carbide (CaC₂) enables the reaction of its ethynyl moiety with organic electrophiles. This was realized simply by co-milling CaC₂ with organic substrates in a sealed jar without the need for an additive or a catalyst. Various ketones including those bearing α-hydrogens were ethynylated in good yields at short reaction times. Aryl halides are also amenable substrates for this protocol as they furnish aryl ethynes through a benzyne intermediate. This method offers a practical and cheap alternative to the established procedures for introducing ethynyl functionalities. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Name: Phenyl(pyridin-2-yl)methanone).

Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Name: Phenyl(pyridin-2-yl)methanone

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem